potassium carbonate in acetone 3 h; Heating;

2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene 1 h; Heating;

1: 72 percent / K2CO3 / acetone / 5 h / Heating 2: 70 percent / N,N-diethylaniline / 3 h / Heating 3: 90 percent / CH3COONa / 1 h / Heating 4: 70 percent / Br2, acetic acid / 0.5 h / Ambient temperature 5: 43 percent / 5percent KOH / ethanol / 2 h / Heating 6: 56 percent / K2CO3 / acetone / 3 h / Heating View Scheme

1: 43 percent / 48 h / 150 °C 2: 1) conc. H2SO4, NaNO2, 2) 10 M H2SO4 / 1) H2O, 0 deg C, 2) 10 min, reflux 3: 72 percent / K2CO3 / acetone / 5 h / Heating 4: 70 percent / N,N-diethylaniline / 3 h / Heating 5: 90 percent / CH3COONa / 1 h / Heating 6: 70 percent / Br2, acetic acid / 0.5 h / Ambient temperature 7: 43 percent / 5percent KOH / ethanol / 2 h / Heating 8: 56 percent / K2CO3 / acetone / 3 h / Heating View Scheme

1: 1) conc. H2SO4, NaNO2, 2) 10 M H2SO4 / 1) H2O, 0 deg C, 2) 10 min, reflux 2: 72 percent / K2CO3 / acetone / 5 h / Heating 3: 70 percent / N,N-diethylaniline / 3 h / Heating 4: 90 percent / CH3COONa / 1 h / Heating 5: 70 percent / Br2, acetic acid / 0.5 h / Ambient temperature 6: 43 percent / 5percent KOH / ethanol / 2 h / Heating 7: 56 percent / K2CO3 / acetone / 3 h / Heating View Scheme

1: 55 percent / 20 h / 150 °C 2: 72 percent / K2CO3 / acetone / 5 h / Heating 3: 70 percent / N,N-diethylaniline / 3 h / Heating 4: 90 percent / CH3COONa / 1 h / Heating 5: 70 percent / Br2, acetic acid / 0.5 h / Ambient temperature 6: 43 percent / 5percent KOH / ethanol / 2 h / Heating 7: 56 percent / K2CO3 / acetone / 3 h / Heating View Scheme

1: 14 percent / HI (57percent) / acetic acid / 20 h / 65 °C 2: 81 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / toluene / 1 h / Heating View Scheme

potassium hydroxide; potassium carbonate 1) EtOH, reflux, 3 h, 2) acetone, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;